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Preparation method for tricyclic core skeleton of cycloheptatrienone natural product

A technology for cycloheptatrienone and natural products is applied in the field of preparation of the tricyclic core skeleton of cycloheptatrienone natural products, which can solve the problems of expensive reagents, cumbersome operations, long synthesis steps and the like, and achieves short and efficient strategies, high efficiency, high efficiency, and high efficiency. Efficient construction, overcoming the effects of long synthesis steps

Inactive Publication Date: 2019-12-31
SHENZHEN ELDERLY MEDICAL RES INST +1
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Problems solved by technology

It overcomes the technical problems of long synthetic steps, cumbersome operation and expensive reagents in the prior art, resulting in high cost

Method used

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  • Preparation method for tricyclic core skeleton of cycloheptatrienone natural product
  • Preparation method for tricyclic core skeleton of cycloheptatrienone natural product
  • Preparation method for tricyclic core skeleton of cycloheptatrienone natural product

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preparation example Construction

[0028] The preparation method of the compound of formula III of the present invention is to use the compound of formula I as the starting material, and undergo 1,6-conjugate addition / aldol series reaction with the compound of formula II to obtain the target product in one step. The reaction route is as follows:

[0029]

Embodiment 1

[0030] Embodiment 1: the synthesis of formula III compound

[0031] Compound 1 (368 mg, 2 mmol) was dissolved in THF (3 mL), NaH (40 mg, 1 mmol) was added, and after 15 minutes, a THF (2 mL) solution of compound 2 (110 mg, 1 mmol) was added, reacted at room temperature for 3 hours, and saturated chloride was added The reaction was quenched with ammonium aqueous solution, extracted with ethyl acetate, concentrated, and separated on a silica gel column to obtain compound 3 (208 mg, yield 70%).

[0032] 1 H NMR (500MHz, CDCl 3 )δ5.78(s,1H),5.19(s,1H),4.18(dd,J=7.1,5.2Hz,2H),2.81–2.64(m,2H),2.41(s,2H),2.32–2.14 (m,2H),2.07–1.91(m,2H),1.87–1.60(m,3H),1.36–1.29(m,3H),0.98(d,J=6.7Hz,3H).

[0033] 13 C NMR (101MHz, CDCl 3 )δ173.73, 172.31, 168.75, 113.18, 80.35, 76.81, 60.64, 54.94, 32.10, 31.65, 29.59, 27.33, 23.06, 21.94, 17.03, 14.12

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Abstract

The invention discloses a preparation method for a tricyclic core skeleton of a cycloheptatrienone natural product. The preparation method comprises the following steps: carrying out a conjugate addition reaction on a compound as shown in a formula I and a compound shown in a formula II under the action of an alkali to obtain an intermediate A, and isomerizing the intermediate A to obtain an estercarbonyl gamma-site negative ion compound B; and carrying out an aldol reaction on the negative ion compound B and a keto-carbonyl group under an acidic condition to obtain a single-configuration compound as shown in a formula III.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of a tricyclic core skeleton of a tropotrienone natural product. Background technique [0002] The chemical synthesis of complex natural products is playing an increasingly important role in promoting the development of modern medicine. Drugs related to natural products account for a considerable proportion of all kinds of drugs approved for marketing. According to statistics, from 1981 to 2006 , among the approved marketed drugs worldwide, drugs related to natural products account for more than 50% (J. Nat. Prod. 2007, 70, 461.). However, considering the limited natural sources and the protection of the ecological environment, it is particularly important to develop the total synthesis of natural products with important pharmaceutical activities. [0003] In 1978, the Buta research group isolated the diterpenoid cycloheptatrienone compound har...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92
CPCC07D307/92
Inventor 吴正治陶成钱自亮曾嫱姜倩倩李利民陈云芳
Owner SHENZHEN ELDERLY MEDICAL RES INST
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